DE602007006649D1 - Use of esters of organic acids with 5-hydroxymethylfurfural - Google Patents
Use of esters of organic acids with 5-hydroxymethylfurfuralInfo
- Publication number
- DE602007006649D1 DE602007006649D1 DE602007006649T DE602007006649T DE602007006649D1 DE 602007006649 D1 DE602007006649 D1 DE 602007006649D1 DE 602007006649 T DE602007006649 T DE 602007006649T DE 602007006649 T DE602007006649 T DE 602007006649T DE 602007006649 D1 DE602007006649 D1 DE 602007006649D1
- Authority
- DE
- Germany
- Prior art keywords
- esters
- hydroxymethylfurfural
- organic acids
- organic acid
- fuel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
Method for the manufacture of organic acid esters of 5-hydroxymethylfurfural by reacting a fructose or glucose-containing starting material with an organic acid or its anhydride in the presence of a catalytic or sub-stoechiometric amount of solid acid catalyst. The catalysts are heterogeneous and may be employed in a continuous flow fixed bed reactor. The esters can be applied as a fuel or fuel additive.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06075565A EP1834951A1 (en) | 2006-03-10 | 2006-03-10 | Method for the synthesis of organic acid esters of 5-hydroxymethylfurfural and their use |
PCT/EP2007/002146 WO2007104515A1 (en) | 2006-03-10 | 2007-03-12 | Method for the synthesis of organic acid esters of 5-hydroxymethylfurfural and their use |
Publications (1)
Publication Number | Publication Date |
---|---|
DE602007006649D1 true DE602007006649D1 (en) | 2010-07-01 |
Family
ID=36956006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE602007006649T Active DE602007006649D1 (en) | 2006-03-10 | 2007-03-12 | Use of esters of organic acids with 5-hydroxymethylfurfural |
Country Status (13)
Country | Link |
---|---|
US (1) | US8242293B2 (en) |
EP (5) | EP2053047A1 (en) |
JP (1) | JP2009529551A (en) |
CN (1) | CN101421259A (en) |
AT (3) | ATE473218T1 (en) |
AU (1) | AU2007224708B2 (en) |
BR (1) | BRPI0707099A2 (en) |
CA (2) | CA2893566C (en) |
DE (1) | DE602007006649D1 (en) |
MY (1) | MY145760A (en) |
UA (1) | UA98615C2 (en) |
WO (1) | WO2007104515A1 (en) |
ZA (1) | ZA200807984B (en) |
Families Citing this family (76)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102007007629A1 (en) * | 2007-02-16 | 2008-08-21 | Evonik Degussa Gmbh | Process for the preparation of 5-hydroxymethyl furfural via 5-acyloxymethyl furfural as an intermediate |
EP2034005A1 (en) * | 2007-09-07 | 2009-03-11 | Furanix Technologies B.V | Fuel additive concentrate derived from a biomass resource |
EP2183236B1 (en) | 2007-09-07 | 2011-02-16 | Furanix Technologies B.V. | Hydroxymethylfurfural ethers and esters prepared in ionic liquids |
CN101896476A (en) * | 2007-12-12 | 2010-11-24 | 阿彻丹尼尔斯米德兰德公司 | Conversion of carbohydrates to hydroxy-methylfurfural (HMF) and derivatives |
CA2773640C (en) | 2009-10-07 | 2019-09-10 | Furanix Technologies B.V. | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof |
JP5866290B2 (en) * | 2009-10-07 | 2016-02-17 | フラニックス テクノロジーズ ベスローテン フェンノートシャップ | Process for preparing 2,5-furandicarboxylic acid and process for preparing dialkyl ester of 2,5-furandicarboxylic acid |
WO2011129640A2 (en) * | 2010-04-15 | 2011-10-20 | 한국생산기술연구원 | Metal catalyst composition for producing furfural derivatives from raw materials of lignocellulosic biomass, and method for producing furfural derivatives using the composition |
US9024047B2 (en) | 2010-12-21 | 2015-05-05 | E I Du Pont De Nemours And Company | Methods for furfural production from branched non-fermentable sugars in stillage or syrup |
NL2005928C2 (en) * | 2010-12-28 | 2012-07-02 | Furanix Technologies Bv | Process for the conversion of a carbohydrate-containing feedstock. |
FR2975396B1 (en) * | 2011-05-16 | 2013-12-27 | Centre Nat Rech Scient | PROCESS FOR THE PREPARATION OF 5-HYDROXYMETHYLFURFURAL |
US20120302768A1 (en) | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US9573120B2 (en) | 2014-05-08 | 2017-02-21 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US8791278B2 (en) | 2011-05-24 | 2014-07-29 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US8791277B2 (en) | 2011-05-24 | 2014-07-29 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US9199958B2 (en) | 2011-05-24 | 2015-12-01 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US8846960B2 (en) | 2011-05-24 | 2014-09-30 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
CN102326728B (en) * | 2011-06-30 | 2012-12-19 | 山东香驰健源生物科技有限公司 | Method for removing 5-hydroxymethyl furfural (5-HMF) in high-fructose corn syrup (HFCS) |
DE102012200086A1 (en) * | 2011-09-30 | 2013-04-04 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Process for the preparation of furan compounds from renewable raw materials |
PT2574682E (en) * | 2011-09-30 | 2014-01-21 | Kemira Oyj | Environmentally friendly composition, suitable for leather tanning, comprising zeolite |
EP2766351A1 (en) * | 2011-10-12 | 2014-08-20 | Novozymes A/S | Production of 5-hydroxymethylfurfural from fructose using a single-phase mixed aqueous-organic solvent system |
CN102442982B (en) * | 2011-12-06 | 2014-03-19 | 中国科学院青岛生物能源与过程研究所 | Method for preparing furandimethanol dialkyl ether with sugar |
CA2856173A1 (en) | 2011-12-13 | 2013-06-20 | Basf Se | Separating off 5-hydroxymethylfurfural (hmf) from reaction solutions by steam distillation |
US9156802B2 (en) | 2011-12-13 | 2015-10-13 | Basf Se | Separating off 5-hydroxymethylfurfural (HMF) from reaction solutions by steam distillation |
CA2856466A1 (en) | 2011-12-13 | 2013-06-20 | Basf Se | Preparation of 5-hydroxymethylfurfural (hmf) from saccharide solutions in the presence of a solvent having a boiling point greater than 60 degree c and less than 200 degree c (at standard pressure, called low boiler for short) |
US9169227B2 (en) | 2011-12-13 | 2015-10-27 | Basf Se | Production of 5 hydroxymethyulfurfural (HMF) from hexose solutions in the presence of steam |
US9162998B2 (en) | 2011-12-13 | 2015-10-20 | Basf Se | Preparation of 5-hydroxymethylfurfural (HMF) from saccharide solutions in the presence of a solvent having a boiling point greater than 60° C. and less than 200° C. (at standard pressure, called low boiler for short) |
WO2013087613A1 (en) | 2011-12-13 | 2013-06-20 | Basf Se | Preparation of 5-hydroxymethylfurfural (hmf) from hexose solutions in the presence of steam |
US9181210B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Processes for making furfurals |
WO2013102015A1 (en) | 2011-12-28 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of furfural |
WO2013100768A2 (en) | 2011-12-28 | 2013-07-04 | Furanix Technologies B.V. | Process for carrying out a reaction involving a liquid reaction mixture |
BR112014015988A8 (en) | 2011-12-28 | 2017-07-04 | Du Pont | process |
US9181211B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Process for the production of furfural |
BR112014016687A8 (en) * | 2012-01-10 | 2017-07-04 | Archer Daniels Midland Co | process for making hydroxymethylfurfural from an aqueous solution including one or more hexoses and process for making hydroxymethylfurfural ether from an aqueous solution including one or more hexoses |
KR101374219B1 (en) | 2012-03-18 | 2014-03-13 | 서울대학교산학협력단 | Novel method for preparing 5-acetoxymethylfurfural using alkylammonium acetate salts |
US8748479B2 (en) | 2012-06-22 | 2014-06-10 | Eastman Chemical Company | Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation |
US8969404B2 (en) | 2012-06-22 | 2015-03-03 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
US9029580B2 (en) | 2012-07-20 | 2015-05-12 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US8809556B2 (en) | 2012-07-20 | 2014-08-19 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US8772513B2 (en) | 2012-08-30 | 2014-07-08 | Eastman Chemical Company | Oxidation process to produce a crude dry carboxylic acid product |
NL2009674C2 (en) | 2012-10-22 | 2014-04-23 | Furanix Technologies Bv | Process for the preparation of benzene derivatives. |
CN102911142B (en) * | 2012-10-24 | 2015-04-22 | 复旦大学 | Method for preparing 5-hydroxymethylfurfural |
US8916719B2 (en) | 2012-11-20 | 2014-12-23 | Eastman Chemical Company | Process for producing dry purified furan-2,5-dicarboxylic acid with oxidation off-gas treatment |
US9156805B2 (en) | 2012-11-20 | 2015-10-13 | Eastman Chemical Company | Oxidative purification method for producing purified dry furan-2,5-dicarboxylic acid |
US8916720B2 (en) | 2012-11-20 | 2014-12-23 | Eastman Chemical Company | Process for producing dry purified furan-2,5-dicarboxylic acid with oxidation off-gas treatment |
MX354363B (en) * | 2013-03-14 | 2018-02-27 | Archer Daniels Midland Co | Process for making hmf from sugars with reduced byproduct formation, and improved stability hmf compositions. |
WO2014197195A2 (en) | 2013-06-06 | 2014-12-11 | California Institute Of Technology | Diels-alder reactions catalyzed by lewis acid containing solids: renewable production of bio-plastics |
EP2813494A1 (en) | 2013-06-12 | 2014-12-17 | Basf Se | Method for the preparation of 5-hydroxymethylfurfural (HMF) |
DE102013106530A1 (en) * | 2013-06-21 | 2014-12-24 | Christoph Pallua | cancer drug |
DE102013223496A1 (en) | 2013-11-18 | 2015-05-21 | Tesa Se | Novel polyester suitable for the production of carrier materials for adhesive tapes |
BR112016016751B1 (en) | 2014-01-27 | 2021-08-31 | Archer-Daniels-Midland Company | PROCESS FOR THE PRODUCTION OF A PRODUCT THAT INCLUDES HMF AND WATER |
US9943834B2 (en) | 2014-05-08 | 2018-04-17 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9388351B2 (en) | 2014-06-18 | 2016-07-12 | Phillips 66 Company | Furfural to fuel |
KR101671770B1 (en) * | 2014-09-02 | 2016-11-03 | 한국생산기술연구원 | A novel method for preparing 5-acetoxymethylfurfural using microwave |
EP3221301A4 (en) * | 2014-11-21 | 2018-04-18 | Archer Daniels Midland Company | Acid-catalyzed acylation of 5-(hydroxylmethyl)-furfural reduction products |
EP3256513B1 (en) | 2015-02-10 | 2021-10-27 | Furanix Technologies B.V. | Fuel composition comprising humins |
CA2990580C (en) | 2015-07-01 | 2020-01-28 | Synvina C.V. | Process for the preparation of a furfural derivative |
MX2018000198A (en) * | 2015-07-01 | 2018-04-11 | Synvina C V | Process for the preparation of a furfural derivative comprising neutralizing an acid reaction mixture. |
EP3337790A4 (en) * | 2015-08-21 | 2019-01-23 | GFBiochemicals Limited | Process to prepare hydroxymethylfurfural derivatives |
WO2017074183A1 (en) | 2015-10-26 | 2017-05-04 | Vantium Knowledge Centre B.V. | Humins-containing foam |
EP3371161A1 (en) | 2015-11-04 | 2018-09-12 | Basf Se | A process for preparing furan-2,5-dicarboxylic acid |
WO2017076947A1 (en) | 2015-11-04 | 2017-05-11 | Basf Se | Process for preparing furan-2,5-dicarboxylic acid |
JP2018536656A (en) | 2015-11-04 | 2018-12-13 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Process for preparing a mixture comprising 5- (hydroxymethyl) furfural and certain HMF esters |
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KR20180107143A (en) | 2016-01-13 | 2018-10-01 | 스토라 엔소 오와이제이 | Process for preparing 2,5-furandicarboxylic acid and its intermediates and derivatives |
WO2018062995A1 (en) | 2016-09-29 | 2018-04-05 | Avantium Knowledge Centre B.V. | Process for the modification of humins |
WO2018135941A1 (en) | 2017-01-17 | 2018-07-26 | Avantium Knowledge Centre B.V. | Asphalt composition comprising humins obtained from dehydration of carbohydrates |
JP7158462B2 (en) | 2017-07-12 | 2022-10-21 | ストラ エンソ オーユーイー | Purified 2,5-furandicarboxylic acid pathway product |
WO2019122385A1 (en) | 2017-12-22 | 2019-06-27 | Avantium Knowledge Centre B.V. | A fibre |
EP3810583B1 (en) * | 2018-06-22 | 2024-04-03 | Council of Scientific and Industrial Research | Process for 5-hydroxymethylfurfural (5-hmf) synthesis from carbohydrates |
CN109111414B (en) * | 2018-09-06 | 2020-11-06 | 沈阳化工大学 | Method for converting agarose to co-produce 5-hydroxymethylfurfural and levulinic acid |
CN110152743B (en) * | 2019-06-19 | 2020-06-09 | 中国科学院大连化学物理研究所 | Solid acid catalyst and application thereof in supercritical CO2Application of synthesizing 5-hydroxymethylfurfural in methanol system |
CN112830907B (en) * | 2019-12-20 | 2022-03-22 | 中国科学院宁波材料技术与工程研究所 | Method for preparing 5-hydroxymethylfurfural |
CN111057594B (en) * | 2019-12-30 | 2021-10-29 | 李旭 | Preparation method of alcohol-based fuel additive |
WO2023066577A1 (en) | 2021-10-21 | 2023-04-27 | Furanix Technologies B.V. | Process for the preparation of a furfural derivative |
WO2023166503A1 (en) | 2022-03-01 | 2023-09-07 | Celluflux Ltd. | Synthesis of 5-acetoxymethyl furfural in the presence of recyclable salt catalysts |
CN117069869B (en) * | 2023-10-17 | 2024-01-02 | 山东力宏宝冠纤维素有限公司 | Flexible carboxymethyl cellulose ether, preparation method thereof, negative electrode plate and battery |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US925812A (en) * | 1909-01-26 | 1909-06-22 | Watson & Mcdaniel Company | Fluid-pressure regulator. |
NL111819C (en) * | 1957-10-11 | |||
GB925812A (en) * | 1958-09-05 | 1963-05-08 | Merck & Co Inc | Novel ester of hydroxymethylfurfural and process for its preparation |
US4339245A (en) * | 1980-10-24 | 1982-07-13 | Phillips Petroleum Company | Motor fuel |
DE3502802A1 (en) * | 1985-01-29 | 1986-07-31 | Ernst 7504 Weingarten Kirchgässner | Process for improved and environmentally sounder utilisation of motor fuels |
DE3601281A1 (en) | 1986-01-17 | 1987-07-23 | Sueddeutsche Zucker Ag | METHOD FOR PRODUCING 5-HYDROXYMETHYLFURFURAL, INCLUDING A CRYSTALINE PRODUCT, WITH THE EXCLUSIVE USE OF WATER AS A SOLVENT |
DE3621517A1 (en) * | 1986-06-27 | 1988-01-07 | Klaus Dipl Chem Dr Garves | Synthesis of alkoxymethylfurfurals and alkyl levulinates from cellulose or lignocelluloses or starch and alcohols |
FR2670209B1 (en) | 1990-12-07 | 1995-04-28 | Commissariat Energie Atomique | PROCESS FOR THE PREPARATION OF FURFURAL HYDROXYMETHYL-5 BY HETEROGENEOUS CATALYSIS. |
US6603026B2 (en) * | 2001-08-07 | 2003-08-05 | Gene E. Lightner | Heterocyclic compounds produced from biomass |
-
2006
- 2006-03-10 EP EP09151758A patent/EP2053047A1/en not_active Withdrawn
- 2006-03-10 EP EP06075565A patent/EP1834951A1/en not_active Withdrawn
- 2006-03-10 AT AT09151759T patent/ATE473218T1/en not_active IP Right Cessation
- 2006-03-10 EP EP09151759A patent/EP2050742B1/en not_active Not-in-force
-
2007
- 2007-03-12 BR BRPI0707099-3A patent/BRPI0707099A2/en not_active IP Right Cessation
- 2007-03-12 AT AT07723191T patent/ATE468330T1/en not_active IP Right Cessation
- 2007-03-12 MY MYPI20083490A patent/MY145760A/en unknown
- 2007-03-12 JP JP2008558698A patent/JP2009529551A/en active Pending
- 2007-03-12 EP EP07723191A patent/EP2001859B1/en not_active Not-in-force
- 2007-03-12 CA CA2893566A patent/CA2893566C/en not_active Expired - Fee Related
- 2007-03-12 AT AT09165171T patent/ATE529416T1/en not_active IP Right Cessation
- 2007-03-12 WO PCT/EP2007/002146 patent/WO2007104515A1/en active Search and Examination
- 2007-03-12 DE DE602007006649T patent/DE602007006649D1/en active Active
- 2007-03-12 CA CA2645060A patent/CA2645060C/en not_active Expired - Fee Related
- 2007-03-12 CN CNA2007800083549A patent/CN101421259A/en active Pending
- 2007-03-12 EP EP09165171A patent/EP2105439B1/en not_active Revoked
- 2007-03-12 AU AU2007224708A patent/AU2007224708B2/en not_active Ceased
- 2007-03-12 US US12/282,288 patent/US8242293B2/en active Active
- 2007-12-03 UA UAA200811992A patent/UA98615C2/en unknown
-
2008
- 2008-09-17 ZA ZA200807984A patent/ZA200807984B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CN101421259A (en) | 2009-04-29 |
EP2105439A1 (en) | 2009-09-30 |
CA2645060C (en) | 2015-10-06 |
EP2050742A1 (en) | 2009-04-22 |
EP1834951A1 (en) | 2007-09-19 |
EP2050742B1 (en) | 2010-07-07 |
JP2009529551A (en) | 2009-08-20 |
EP2105439B1 (en) | 2011-10-19 |
UA98615C2 (en) | 2012-06-11 |
ATE529416T1 (en) | 2011-11-15 |
ZA200807984B (en) | 2009-10-28 |
CA2893566C (en) | 2016-08-02 |
CA2645060A1 (en) | 2007-09-20 |
MY145760A (en) | 2012-04-13 |
BRPI0707099A2 (en) | 2011-04-19 |
AU2007224708B2 (en) | 2011-10-06 |
CA2893566A1 (en) | 2007-09-20 |
US8242293B2 (en) | 2012-08-14 |
EP2001859B1 (en) | 2010-05-19 |
EP2001859A1 (en) | 2008-12-17 |
US20090306415A1 (en) | 2009-12-10 |
AU2007224708A1 (en) | 2007-09-20 |
ATE473218T1 (en) | 2010-07-15 |
EP2053047A1 (en) | 2009-04-29 |
ATE468330T1 (en) | 2010-06-15 |
WO2007104515A1 (en) | 2007-09-20 |
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